(6-BROMO-1H-INDOL-2-YL)METHANOL

(6-BROMO-1H-INDOL-2-YL)METHANOL Property

Melting point:

111-113°

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Safety

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

(6-BROMO-1H-INDOL-2-YL)METHANOL Chemical Properties,Usage,Production

Chemical Properties

White to light yellow powder or solid

Synthesis

General procedure for the synthesis of (6-bromo-1H-indol-2-yl)methanol from 6-bromoindole-2-carboxylic acid: to a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in tetrahydrofuran (THF, 20.0 mL) was added slowly and dropwise at 0 °C lithium aluminium hydroxide (LiAlH4, 1.0 M solution in THF, 4.20 mL. 4.20 mmol). The reaction mixture was gradually warmed to room temperature with stirring for 4 hours. Upon completion of the reaction, the reaction was quenched by sequential addition of water and 15% aqueous sodium hydroxide (NaOH) solution at 0°C, at which time a precipitate was generated. The reaction mixture was filtered through a diatomaceous earth pad and the filtrate was extracted with ethyl acetate (EtOAc, 3 x 20 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the target product (6-bromo-1H-indol-2-yl)methanol (696 mg, 73% yield) as a yellow solid. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 7.51 (s, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.20 (dd, J=8.0,1.6 Hz, 1H), 6.38 (s, 1H), 4.83 (d, J=5.6 Hz, 2H).

References

[1] Liebigs Annalen der Chemie, 1986, # 3, p. 438 - 455
[2] Patent: US2012/157469, 2012, A1. Location in patent: Page/Page column 28-29
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 2, p. 364 - 377